p-Methoxybenzyl ether cleavage by polymer-supported sulfonamides

Organic Letters
Ronald J Hinklin, Laura L Kiessling

Abstract

[reaction: see text] p-Methoxybenzyl ethers have been found to transfer from alcohols to sulfonamides in the presence of catalytic trifluoromethanesulfonic acid. This process for protecting group removal can be performed in solution with yields >94%. Through the use of sulfonamide-functionalized ("safety-catch") resins, p-methoxybenzyl ethers can be cleaved in excellent yields with minimal purification.

References

Jul 18, 2001·Journal of the American Chemical Society·R J Hinklin, L L Kiessling
Nov 1, 1996·The Journal of Organic Chemistry·D J JenkinsB V Potter

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Citations

Sep 22, 2009·The Journal of Organic Chemistry·Xiaowei LuXuefei Huang
Mar 25, 2011·Chemical Communications : Chem Comm·Joseph W TuckerCorey R J Stephenson
Sep 26, 2012·The Journal of Organic Chemistry·Nicolas KernPatrick Pale
Nov 1, 2016·Organic Letters·Agnete H ViuffHenrik H Jensen
Apr 5, 2017·Organic Letters·Robert A GreenRichard C D Brown
May 24, 2003·The Journal of Organic Chemistry·Gangavaram V Madhava SharmaPalakodety Radha Krishna
Nov 11, 2003·Journal of Combinatorial Chemistry·Roland E Dolle

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